Orotic Acid Derivative Condensation with Two-Phase Separation
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Solution Overview
Problem
Conventional methods for producing orotic acid derivatives are not suitable for industrial implementation due to high reagent costs, the use of halogenic solvents, and the need for column chromatography, leading to inefficiencies and high production costs.
Innovation Solution
A method involving a condensation reaction between orotic acid halide and glutamic acid under basic conditions using a two-phase solvent system of water and an organic solvent, followed by neutralization crystallization to separate the orotic acid derivative without column chromatography, utilizing inexpensive reagents and simple filtration.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If conventional active esterification method is used, then orotic acid derivative can be synthesized, but reagent cost is high and column chromatography is required for purification
Solution Approach 1:
The invention extracts and removes the problematic purification step (column chromatography) from the synthesis process by designing a reaction system where byproducts are automatically separated through phase partitioning, leaving only simple filtration as the purification method
Solution Approach 2:
The invention introduces a two-phase solvent system (organic phase and aqueous phase) as an intermediary medium that facilitates automatic separation of byproducts from the target orotic acid derivative, eliminating the need for complex column chromatography purification
2Productivity
If dichloromethane is used as reaction solvent, then condensation reaction proceeds, but halogenic solvent makes the method unsuitable for industrial implementation
Solution Approach 1:
The invention replaces the expensive and environmentally problematic dichloromethane solvent with cheaper, environmentally friendly alternative solvents (such as ethyl acetate, n-butyl acetate, or their mixtures with water), making the process suitable for industrial implementation while maintaining reaction efficiency
Solution Approach 2:
The invention changes the solvent parameters from halogenic to non-halogenic solvents, and optimizes the solvent system to a two-phase mixture that maintains adequate solubility for the reaction while enabling easy phase separation for purification
3Ease of operation
If orotic acid is used in organic solvent, then activation of carboxy group can occur, but low solubility causes decrease in reaction rate
Solution Approach 1:
The invention changes the solvent parameters from single-phase organic solvent to two-phase solvent system, which improves the solubility of orotic acid through the aqueous phase while maintaining the organic phase for reaction activation, thereby increasing reaction rate without sacrificing reaction capability
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
This method enables the production of highly purified orotic acid derivatives at a lower cost and with improved industrial feasibility by avoiding costly reagents and complex purification steps, allowing for efficient separation and high yield.
Implementation Method 1
a two-phase solvent system of water and an organic solvent
Implementation Method 2
followed by neutralization crystallization to separate the orotic acid derivative without column chromatography
Implementation Method 3
a neutralization crystallization step of precipitating crystals of orotic acid by neutralization crystallization to separate a liquid containing the orotic acid derivative from the crystals of orotic acid
Implementation Method 4
precipitating crystals of orotic acid by neutralization crystallization
Implementation Method 5
a condensation step of performing, under a basic condition, a condensation reaction between an orotic acid halide and a compound to generate an orotic acid derivative
Data Source
AI summary
Provided is a method for producing an orotic acid derivative, the method comprising a condensation step of performing, under a basic condition, a condensation reaction between an orotic acid halide represented by General Formula (I) and a compound represented by General Formula (II) to generate an orotic acid derivative represented by General Formula (III) ; and a neutralization crystallization step of precipitating crystals of orotic acid by neutralization crystallization to separate a liquid containing the orotic acid derivative from the crystals of orotic acid, after the condensation step. In General Formula (I), (II), or (III), X is a halogen atom, and A is a group represented by General Formula (A-1) or (A-2). In General Formula (A-1) or (A-2), R1 is a hydrogen atom or an organic group, and R2 and R3 are each independently an organic group. In a case where R1 is an organic group, R1 and R2 may be bonded to each other to form a ring.